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14343

Sigma-Aldrich

1(S),9(R)-(−)-Bicuculline methiodide

≥95.0% (HPCE)

Synonyme(s) :

(5S)-5-[(6R)-6,8-Dihydro-8-oxofuro[3,4-e]-1,3-benzodioxol-6-yl]-5,6,7,8-tetrahydro-6,6-dimethyl-1,3-dioxolo[4,5-g]isoquinolinium iodide

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About This Item

Formule empirique (notation de Hill):
C21H20INO6
Numéro CAS:
40709-69-1
Poids moléculaire :
509.29
Numéro Beilstein :
5419649
Numéro MDL:
MFCD00078966
Code UNSPSC :
12352200
ID de substance PubChem :
329750456
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥95.0% (HPCE)

Forme

powder

Activité optique

[α]/D -117±7°, c = 1 in chloroform

Solubilité

H2O: 10 mg/mL, almost clear, greenish-yellow

Température de stockage

2-8°C

Chaîne SMILES 

[I-].[H][C@]1(OC(=O)c2c3OCOc3ccc12)[C@]4([H])c5cc6OCOc6cc5CC[N+]4(C)C

InChI

1S/C21H20NO6.HI/c1-22(2)6-5-11-7-15-16(26-9-25-15)8-13(11)18(22)19-12-3-4-14-20(27-10-24-14)17(12)21(23)28-19;/h3-4,7-8,18-19H,5-6,9-10H2,1-2H3;1H/q+1;/p-1/t18-,19+;/m0./s1

Clé InChI

HKJKCPKPSSVUHY-GRTNUQQKSA-M

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Description générale

Bicuculline is a phthalide isoquinoline alkaloid, which is extracted from Dicentra cucullaria. It acts as an acetylcholinesterase inhibitor. Bicuculline inhibits slow afterhyperpolarization (AHP).

Application

1(S),9(R)-(-)-Bicuculline methiodide has been used as a gamma-aminobutyric acid (GABA) antagonist to block inhibition in the semicoronal slices. It has also been used for the preparation of organotypic hippocampal slice cultures (OHSCs).

Actions biochimiques/physiologiques

(-)-Bicuculline methiodide is a GABAA receptor antagonist, which acts as a competitive inhibitor of GABA ligand binding to the receptor.

Caractéristiques et avantages

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the GABAA Receptors and Potassium Channels pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Notes préparatoires

hergestellt aus (+)-Bicucullin

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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